St Maarten Itinerary for A Weekend Getaway

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A few years ago, Dan surprised me with a trip. “Guess where I’m taking you for your birthday weekend?”

He smiled at my clueless look. “Here’s a hint: It’s in the Caribbean.”


Hill in St Maarten, Netherlands Antilles with palm tree in foreground

“No, but that’s a good guess because we’ve been wanting to visit.”


“Nope, further north. Here’s another hint: They speak two languages there and you’ve been to both of their mother countries.”

“Oh, we’re going to spend a weekend in Sint Maarten and Saint Martin! That’ll be fun, thank you!”

“You’re welcome. Maybe you’ll get to use your French while we’re there.”

“I’d like that, and maybe I can even use the three Dutch words I know.”

Here’s our loosely-planned St. Maarten itinerary. There are a lot of reasons to visit Saint Martin, so maybe it will inspire you to plan a weekend getaway of your own!


Noontime arrival in St Maarten

We left on Friday morning, arriving at Princess Juliana International Airport in time for a late lunch. The sun teased us as we rode to the hotel, making the ocean sparkle and creating assorted luminous green and blue hues that Crayola will never be able to duplicate.


Ocean and inlets with St Maarten hotels in the background

Checking out the hotel and surrounds

It’s always fun to see what a hotel has to offer, and that’s the first thing we did after checking in. As soon as I saw they had an assortment of restaurants, three pools, a swim-up bar, and free wi-fi, I was one happy birthday girl.

Our room at Divi Little Bay Beach Resort had a balcony that overlooked a beautiful white sand beach and offered a panoramic view. Cliffs rose to the left and right and down on the sand, a row of lounge chairs and umbrellas awaited guests.

Time to get some lunch, so we chose the beachside bar. The better to admire the view with, my dear.

As we ate, Dan noticed a nearby hill. “I want to hike up there before we leave,” he said, “just to see what’s on the other side.” It sounded intriguing, although I suspected we would just see more ocean.

Still, there’s nothing wrong with that.

2 people on a St Maarten beach

But first, sightseeing in St Maarten.

Afternoon segway tour of Philipsburg

My thoughtful husband had planned an afternoon surprise: a Segway tour of Philipsburg. I was thrilled! Little did he know that I had wanted to ride a Segway for a long time.

I figured it couldn’t be too hard to learn, because the security guards ride them around our local malls effortlessly. I was right: After only a few minutes of instruction, we were both riding like pros.

Woman on a segway in St Maarten

Our tour was only on the wide, paved boardwalk, so we rode past hotels, restaurants, bars, and kitschy souvenir stands. At one end the boardwalk ends in a wide, sandy beach; at the other, not far from the cruise port, it terminates at a beautiful marina and shopping area.

The tour was fun, but learning to ride a Segway was even better. I want one!

Marina in Sint Maarten

Exploring Philipsburg on foot

St. Maarten’s capital, Philipsburg, is little more than three parallel roads, all connected by a few side streets that are popular with tourists.

Tourists on a pedestrian side street in Philipsburg. Sign overhead says Old Street Sint Maarten.
Old Street is a pedestrian side street.
Quiet back street in Philipsburg.
Back street has shops that appeal to locals.

You have the boardwalk, Front Street, and Back Street. They may not be the most creative names, but what difference? They make sense.

  • Front Street is closer to the beach and tourist area. With restaurants, boutiques and jewelry stores, this is the higher rent district.
  • Back Street is set “back” from the beach. This is where most of the local needs can be found (think household goods and food markets, for instance).
Building with a tower in background. Palmtree and clock in foreground.
Philipsburg courthouse

Beachside drinks and a beautiful sunset

Even though the boardwalk has plenty of bars, Phillipsburg itself is pretty dead after working hours. We asked a taxi driver to take us to a bar where we could watch the sun set.

He dropped us off Simpson Bay. We walked along the sand until we found a bar that offered a terrace view of the sunset. Dan took some birthday portrait shots of me to commemorate our weekend getaway and we watched a few energetic teens perform flips with a bosu ball they’d set in the sand.

Teen in the midst of a flip. Sailboats in the background.

Two little boys with wild imaginations played at being pirates next to our table, and a hawker eagerly promoted a “free giveaway in just a few minutes” over a loudspeaker.

As watched the sky change colors behind the sailboats bobbing on the calm water, we fantasized about sailing all the islands in the Caribbean. (We never did find out what the hawker was giving away. The “few minutes” he promised lasted long past sunset.)

Of course, a Caribbean sunset is always spectacular!

Sailboats silhouetted against a colorful sunset in St Maarten

Boats on the water in St Maarten

Fresh seafood at a waterside restaurant

Few things can get us as excited as the opportunity to try local food. Islands usually offer ocean bounty, so we both chose fresh fish from a menu that did not disappoint.

Scotch Bonnet peppers (aka habaneros) are part of the island’s cuisine, so Dan took advantage of it. Not having an asbestos tongue, I steered clear of the spicy creole but still … it smelled heavenly.

Quaint aqua cafe along the water in St Maarten


Morning snorkeling in St. Martin

There’s nothing like seeing a beautiful Caribbean island from the water, so Saturday morning was devoted to snorkeling and and sightseeing around Sint Maarten. If that sounds like fun to you, we suggest you either use the company we used or Viator’s Ultimate Eco Tour. Both have excellent reviews.

Either way, everything is arranged: transportation to/from the dock, the snorkeling equipment, food, drinks, everything. All we needed to bring was a towel and sunscreen.

TIP: You’ll run less of a chance of a sunburn if you book a morning tour. Afternoon sun can be especially strong.

As we went from place to place, we enjoyed sandwiches on fresh baguettes, chips and salsa, fruit salad, and a delicious homemade rum punch. Wish I’d asked for the recipe.

People on the deck of a boat eating and drinking

Captain Alan had warned us at the outset that our snorkeling sites would depend on water and weather conditions. We only got to snorkel in St. Maarten that day, but all the locations were excellent. The boat took us to some wonderful spots, with reefs, a sand bar to wade on, and lonely beaches to explore.

Sailboats on the water, hills in background and a sandbar in the foreground

Our captain advised us on the best way to enjoy each spot – where to head and what to see – and at one stop he took the more adventurous ones to a deeper area where sea turtles like to swim. Of course we went, as I had long wanted to see turtles in the open water.

We did it! We saw turtles! We also saw an octopus, conch, a stingray, and many of the fish and corals that we had once had in our saltwater aquarium at home.

Coral seen while snorkeling in St Maarten

Afternoon exploring the area

When we got back to the hotel, Dan finally got his chance to climb that nearby hill. I’d had enough sun with my super-fair skin, so I waved him goodbye from a shady spot.

He came back happy, with a camera full of photos of local wildlife, incredible views, and stories of a semi-forgotten cannon that he discovered on the hilltop.

Lizard on a leaf
Old cannon on a hill in St Maarten

Other things to do in St. Martin

There are so many things to do in Sint Maarten/Saint Martin. Tops on our list of things we wish we’d had time for were to visit the French side, as well as:

We want to go back and do those … and now we have a goal to visit every Caribbean island country. Problem is, there are so many islands to choose from that it’s hard to decide where to go first!

Find places to stay in Sint Maarten

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Written by Linda

Linda is multilingual and has been to over 50 countries. Her insatiable love of travel, cuisine, and foreign languages inspired her to create As We Saw It, where she documents her trips, shares practical itineraries, and offers insider tips. She's passionate about helping fellow travelers save time, money, and hassle, and loves to discover new places to explore.

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